Leaders rarely think or speak for themselves.

In climbing the corporate ladder or building a business from scratch, courage turns to cowardice as leaders trade their backbones for a higher perch.

When you found your own business or entity of any sort, you also get to construct the culture that you want to operate within; one that you believe is conducive to a successful and thriving business or other type of endeavor; and one that you want to be a part of.

Which is why I do not understand these founder/owner types who cow to employees and the mob and the latest thing, even if they don’t support it. At least part of the point of creating your own thing, is to make it your own. And that means the brand/business but also the work culture.

But most executives and leaders — whether in businesses they found or those they join — trade in their spines and swap their courage in exchange for another rung on the ladder.

I’ve been thinking a lot about this lately as I endeavor to start my own thing. I am attempting to bolster myself now, in the event of success, to continue to build a brand and a culture that I can be proud of.

I understand that as a business grows, and there are more and more employees and investors, it is more difficult and even perhaps ill-advised to be too stubborn about your own vision. You need to know where to hold the line, and where to accept input and feedback.

And I love input and feedback. Usually — in business — an idea gets better and stronger as you discuss it and build upon it with others. And I love that process. Taking the seed of an idea then bringing in a bunch of smart people with different areas of expertise to make it bigger and better.

But too many owner/founders forget why they started a thing in the first place, as they grow more and more successful. They forget how to be painfully stubborn. They get coached and prodded and they no longer remember the grit and clarity of vision and purpose it took to get a thing off the ground. They no longer know what they think. They know what they are told to think and how they are told to behave to be more leader-like.

Only it’s not leader-like. It’s cowardly and conformist. But the world applauds because they meet the expectations of a leader. They fit the shape of a thing — dignified CEO. Or whatever role they are attempting to play. And the applause and headlines fuel the impetus to conform.

It does seem founders can become just like other executives leading companies or enterprises (e.g. non-profits, universities, etc) in this regard. No longer steadfast and stubborn nor defiant and unyielding. Rather, they become lackeys in their own organizations, falling prey to the direction and pressure of bureaucrats, advisors and employees. They become fearful and pliant rather than fearless and uncompromising.

There aren’t that many executives of note that resist this impulse. And usually the press ends up hating them for not playing their part well.

The press embraces feigned eccentricity and non-conformity as genius! Like that of Elizabeth Holmes. She was lauded and praised as an unconventional mastermind with no real evidence of actual genius. In her case the genius was assumed to be there as the inverse of her kookiness. Same with SBF. And so many others.

But the press actually loathes non-conformity, eccentricity and authenticity in real life form. Because it is difficult and often unpleasant to be around.

It is — at least in part — why there is this torrent of animosity towards Elon Musk — from both the press and regular folks.

He’s supposed to fit the shape of a CEO, abide by the rules of CEO-ness. And he is refusing.

Musk curses on stage at The New York Times DealBook Summit telling advertisers: “Go Fuck Yourself”; he DJ’s Twitter/X — running around (virtually) and commenting on all manner of everything; and he says dumb stuff sometimes that isn’t scripted.

He also “moves fast and breaks things” as Mark Zuckerberg famously said of how to succeed in tech. This phrase is thrown around a lot in more traditional sector companies, as they are envious of the lightening in a bottle some tech start ups seem to harness by adhering to this ethos.

But when Musk does it — I mean really does it like with X — it is deemed reckless.

Musk’s willingness to really move fast and break things is in stark contrast to traditional CEOs in traditional companies who like to say move fast and break things and pretend to do so in order to seem bold, but really are just as mired in bureaucracy and slowness as ever. For them, it’s a branding exercise not a behavioral one.

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At the 2023 World Government Summit, Musk encouraged leaders to speak in their own voices.

"I think it's good for people to speak in their voice, as opposed to how they think they should speak [. . .] It ends up sounding somewhat stiff and not real.”

Musk then pointed out that press releases from corporations can often "sound like propaganda." True.

I’m not some fawning Musk fan. I’m guessing he acts like a real asshole sometimes. I mean we get peeks of it, and I’m imagining a pretty explosive temper replete with inappropriate name-calling bordering on harassment and definitely bullying. I wouldn’t want to work for the man but as much as it sounds terrible to be on the other side of, there is something I deeply respect about refusing to change despite the pressure of expectations for what it means to be and seem like a CEO. To refuse to alter one’s behavior in the face of such persistently negative press and the financial pressure to do so takes real chutzpah. You’d almost have to be insane to do it.

Musk simply refuses to bow down. He speaks in his own voice, always. Which is viewed as dangerous by others (what might he say?) and most people really really don’t like it. They prefer sanitized statements of practiced authenticity from their leaders. Statements that were written by Corporate Communications, then vetted by Human Resources and Legal, and then practiced over and over ad nauseam. That’s what other executives like. That’s what’s the press likes. That’s what consumers like. It’s not scary. And it also never makes them feel lame for not speaking in their own voices.

Coward meet coward.

If you think even founder CEOs aren’t cowering and co-opted, you’d be wrong. I’ve spoken with several founders in the past two years (I’m not going to say their names because they were private conversations and while you may not know their names, you know the brands they started, you’ve heard of the shoes and the food and the clothing) who essentially said:

• Good luck to you in your new endeavors;

• I’ve followed your story closely; well done on having the courage to stand up and say the truth, and accept the great personal risk that came along with that;

• Please forgive me for not doing the same — I’m the breadwinner in my family (yeah, me too) OR I’d lose my business OR OR OR . . . [insert reason here to be a coward].

Now, some founders get ousted by their own boards for refusing to conform. Andrew Crapuchettes is one. He was ousted from his own company, one that he started, for refusing to take stands on social issues in 2020, holding firm to the belief that that was not part of the company’s mission. Then he went out and started another company — Red Balloon, a “woke-free job board.”

But most founders just give in slowly, then all at once, to the shaping of their persona by others, just like other CEOs in traditional companies. They give up a little bit with every positional climb up the ladder or headline or magazine cover that indicates broadening influence. They allow themselves to be contorted by a system that prizes conformity and expectedness, molded to a shape that resembles authenticity but is anything but. And then, after many years, both founder CEOs and executives in more traditional companies no longer know what they think about anything at all, whether it is business related or not. They come to think what they are told they need to say to further the brand and business. Or at least not set it back.

Honestly, it’s pretty much exactly like this video from comedian Ryan Long about Israel and Palestine and what “side to take” for maximum approval:

We saw this in action this past week with the congressional testimonies by the presidents of three prestigious universities: University of Pennsylvania, MIT and Harvard.

When each was asked if calling for the genocide of Jews on college campuses violates the schools’ codes of conduct, they all said the same bullshit thing: well, it depends on context. Clearly, they were prepped by the same PR person, given the same script, and coached to read it in what was supposed to come across as poise, empathy and legal precision but landed as smugness and moral cowardice.

Even the mea culpas the day after from University of Pennsylvania’s Liz Magill and Harvard’s Claudine Gay were scripted, robotic nonsense that conveyed the exact opposite of what they’d said just 24 hours before. So clearly, they didn’t really mean it one of the times. Or both, in all likelihood.

Here’s the thing: I’d wager neither of them even knows what they think on the matter of antisemitism on college campuses. They don’t even know how to determine what they think anymore. What they say is what they are told to say, what their minders predict will be embraced by students and donors and board members and beyond. Which is why, just 24 hours after one statement, they can make one that is the exact opposite without even pausing.

What’s the script? What am I saying? Give it to me now! Do we think this will work? Ok I’m ready!

What they say has nothing to do with what they actually think and it hasn’t for so long they’ve forgotten how to determine what they think. It’s not even part of the equation when choosing to speak.

(Note: As should be obvious, I’ve not spoken with any of them. I’m gleaning this from the obviously scripted statements and my own experience for over 30 years watching executives and leaders in motion.)

All of this is to say, as I start my own brand/business, I’m thinking a lot about committing to not doing any of that. And yes I know successful start ups are a long shot. My ego is not so big that I’m counting on it. In fact, as a long sufferer of imposter syndrome I have to push myself every day to stay optimistic.

I think if I can retain a degree of stubbornness it will increase our chances of actually being successful. And so, I am committing to myself that I will create and stick with furthering a culture of free thinking individuality and merit. I will speak in my own words, which I’ve always done anyway — whether in the books that I write or the speeches that I give now or when I was an executive in the past. I’m committing to saying what I really think. To listening to others but not letting myself get poked and prodded and made to fit the expected shape of a leader.

If I say something stupid, I will apologize.

If I say something smart, rest assured, it’s from my own brain. And if it’s not, I’ll give credit where credit is due.

And I won’t be an asshole, because I’m not one.

And if I fail, it will be because I failed. Not because I let others tell me what I needed to do to be successful.

I would prefer to fail on my own terms than succeed because I sold a part of myself.

Game on.